✦ LIBER ✦
Synthesis of constrained l-phenylalanine derivatives incorporating a benzazepinone or an azepinone ring as VCAM/VLA-4 antagonists
✍ Scribed by Achyutharao Sidduri; Jian Ping Lou; Robert Campbell; Karen Rowan; Jefferson W Tilley
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 96 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Novel constrained L-phenylalanine derivatives incorporating a benzazepinone or an azepinone ring were synthesized in 13 and 8 steps, respectively, employing a key base-catalyzed intramolecular cyclization reaction. The product, 2, was comparable in potency in a VCAM/VLA-4 ELISA assay to the corresponding unconstrained analog 1 suggesting that cyclization favored the bioactive conformation. However, compound 4 was 100-fold less potent than the unconstrained analog 3.